People at UChicago have an eclectic, yet pulled-together style---you definitely don't see people wearing full-body sweatpants all day every day here. Since the weather can be pretty horrid, you see tons of snow boots and long puffer coats, along with Hunter rain boots. Most people seem to have a pretty polished aesthetic, but this question is so hard to answer simply because everyone's style is so varied. UChicago does have more than its fair share of hipsters, though, so think skinny jeans and huge grandpa sweaters, beanies, etc.
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